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Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West...
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Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends.
Experience endless sunshine and the incomparable...
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Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street.
Completely updated for your comfort and convience with new furnitire,...
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May Special $299 a night. This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is...
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The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons.
Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer.
Whether your looking for a place to meditate or find an...
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Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and...
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Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the...
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Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at...
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Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers...
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Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill. At 410 Caroline Street is...
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Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand...
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The Hyatt Windward Pointe is the most luxurious accommodation in Key West. This is one of a kind unit that is the best in the property with ocean and pool view and largest balcony on the third floor. One- king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full...
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Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the...
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The Space
Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset.
Guest Access
You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
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Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in...
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Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in...
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Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy!
If we find that the house has been left excessively dirty,...
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The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers...
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Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped...
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This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main...
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WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships...
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Why stay in one room in a hotel when you can have a whole home? This home has 2 bedrooms, large living room/dining room combination that opens to a deck, and it's own reserved parking space. There is a great community pool that has lots of tropical landscaping and an exercise room in the...
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This studio has been newly remodeled with no expense spared.
Free street parking in front of property and plenty more spots in very close vicinity.
This guest room is cozy (the size of a small hotel room, 10'X12.5') with a QUEEN size bed but is so much better than a hotel room. We provide high...
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Best Deal in Truman Annex - Céad Míle Fáilte (Irish)
2 Bedroom 1 bathroom Condo - sleeps up to 5
Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
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Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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Totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room.
Beautifully decorated by an interior designer. Custom bathrooms and modern kitchen with stainless appliances. Wireless Internet. This is your home...
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You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex.
We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations.
You are in Old Town for convenient entertainment, shopping,...
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Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and free laundry. Take it out for a...
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OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in the heart of Old Town Key West.
Osprey offers all the amenities for two who want a larger space than a hotel room but appreciate the amenities of a vacation rental. Sunny and bright this cottage has...
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The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse...
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Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,...
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Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy!
If we find that the house has been left excessively dirty,...
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Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy!
If we find that the house has been left excessively dirty,...
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Coral Casita - Weekly Vacation Rental
Completely Re-Designed, Re-Decorated and Ready for your island adventures! When Key West is calling your name and nothing else will do, Coral Casita is the perfect mix of location, price and room for your large group to gather.
A spacious 3 bedroom townhome...
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***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo...
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This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between.
Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of French doors that...
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This is a non-smoking condo (smoking on the balcony only) with that "home away from home" appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine...
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Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,...
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Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy!
If we find that the house has been left excessively dirty,...
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Fully furnished cottage home in the heart of old town key west. This place is perfect for a couple as the house is cozy and comfortable. Loft with Queen Bed overlooking the living room. Cathedral ceiling and Hardwood floors. This place has everything you need to live comfortably while steps from...
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ISLAND WIND: When balmy breezes beckon and tropical retreats call your name, Island Wind will be just the escape you need. Located in the pristine gated community of Windward Park this 2 bedroom, 2 bath Bahamian-style townhome is surrounded by lush landscaping and views of a sparkling swimming...
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CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound.
Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with laundry closet. Guest bedroom on the main level with 2 twin beds...
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SHIPYARD TREASURE: 2 bedroom 1 bath Shipyard condo has it all. Located in Truman Annex, there is a shared pool, off street parking and 24 hour security.
Shipyard Treasure is a 2nd floor condo with private full-length balconies front and rear. This property has an open and airy feeling and is one...
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KEY WEST CASA: One of only a few 3 bedroom 2 bath condos in the Shipyard complex in Truman Annex.
Enter the fully stocked kitchen to the living room to the French doors that open onto the back porch. The downstairs bedroom is just to your left and offers 2 twin beds next to the bathroom.
Upstairs...
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Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!

Of course, it’s not all limes and leisure. Phenomenal water activities and outdoor recreation are just steps from your vacation rental, while kid-friendly adventure parks are abundant. The social scene on Duval Street caters to both a younger and older clientele looking to mingle over mouthwatering cuisine or tantalizing cocktails.

Condo rentals in Key West are so enticing that the island is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and it’s been home to literary greats Ernest Hemingway and Tennessee Williams.

Where To Rent a Vacation Home in Key West

Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

Many House Rentals Near Attractions and Activities For All Ages

Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.

Key West Bars and Restaurants

Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

Book a Key West Vacation Rental For Your Next Trip

Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.

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